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Pseudocodeine

From Wikipedia, the free encyclopedia
Pseudocodeine
Names
Systematic IUPAC name
(4R,4aR,5S,7aS,12bS)-9-methoxy-3-methyl-2,4,4a,5,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-5-ol
Other names
  • Neoisocodeine
  • psi-Codeine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.006.711Edit this at Wikidata
UNII
  • InChI=1S/C18H21NO3/c1-19-8-7-18-14-6-4-12(20)16(18)11(19)9-10-3-5-13(21-2)17(22-14)15(10)18/h3-6,11-12,14,16,20H,7-9H2,1-2H3/t11-,12+,14+,16-,18-/m1/s1 checkY
    Key: KYIVACLUFRUFLS-CVXFFHBFSA-N checkY
  • CN1CC[C@]23[C@@H]4C=C[C@@H]([C@H]2[C@H]1CC5=C3C(=C(C=C5)OC)O4)O
Properties
C18H21NO3
Molar mass299.370 g·mol−1
Melting point180 °C (356 °F; 453 K)
Hazards
Lethal dose or concentration (LD, LC):
1,783 mg kg−1(subcutaneous, mouse)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Pseudocodeine is an isomer ofcodeine, once studied for its use as ananalgesic.[1][2] Like codeine, its neighbouring alkene and alcohol groups allow options for functionalisation.[3]

References

[edit]
  1. ^Journal of Pharmacology and Experimental Therapeutics.,55(127), 1935
  2. ^Eddy, Nathan B. (1932)."studies of Morphine, Codeine and Their Derivatives II. Isomers of Codeine".The Journal of Pharmacology and Experimental Therapeutics.45 (3):361–381.doi:10.1016/S0022-3565(25)07960-1.
  3. ^Kalinin, V. N.; Kazantseva, S. A.; Kobak, V. V.; Petrovskii, P. V.; Polyakov, A. V.; Yanovskii, A. I.; Struchkov, Yu. T. (1993-03-02)."ChemInform Abstract: Nucleophilic Substitution in the Allylic System of Codeine and Pseudocodeine. Crystal and Molecular Structure of 8β-Bis( methoxycarbonyl)methyl-8-deoxypseudocodeine".ChemInform.24 (9) chin.199309232.doi:10.1002/chin.199309232.ISSN 0931-7597.
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